CN107793652A - Thin polymer film with changing color resulting from acid and aggregation-induced emission performance and preparation method thereof - Google Patents
Thin polymer film with changing color resulting from acid and aggregation-induced emission performance and preparation method thereof Download PDFInfo
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- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
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- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
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Abstract
Thin polymer film of the present invention with changing color resulting from acid and aggregation-induced emission performance and preparation method thereof, by the way that the organic micromolecule compound with changing color resulting from acid performance and aggregation-induced emission performance and the mixed with polymers with excellent film forming are dissolved, and thin polymer film is made in mixed liquor, wherein, the thin polymer film includes organic micromolecule compound and polymer, it not only has obvious changing color resulting from acid performance and aggregation-induced emission performance, and has excellent film forming；In addition, the preparation method of the thin polymer film, its technique is simple, and it is relatively low to prepare cost.
Description
Technical field
The present invention relates to technical field of organic luminescence materials, and in particular to one kind has changing color resulting from acid and aggregation-induced emission
Thin polymer film of performance and preparation method thereof.
Background technology
Changing color resulting from acid luminescent material refers to that in the case where extraneous acid stimulates its color produces a kind of material substantially changed, in light
Learning the fields such as record, molecule sensing, molecular switch and luminescent device has important potential using value.But traditional acid
There is aggregation fluorescent quenching in mutagens color luminescent material, hinder changing color resulting from acid luminescent material under high concentration or solid state
Practical application in the field such as fluorescent switch and sensor.
2001, this loyal seminar of Tang found molecule aggregation to 1-methyl-1,2,3,4,5-pentaphenyl-
The fluorescent emission of silole (MPPS) compound has positive role.Just the opposite with conventional organic luminescence material, the compound exists
Hardly launch fluorescence in solution, but can but launch strong fluorescence in solid forms.Then they claim this phenomenon
For " aggregation-induced emission " (Aggregation-induced emission, AIE), and this material is called aggregation inducing hair
Luminescent material.AIE fundamentally solves the problem of luminous organic material aggregation inducing quenching, causes in organic light emission research field
Extensive concern.
The mainly organic molecule of changing color resulting from acid gathering induced luminescence material at present, however, in general, it is organic
Small molecule needs that film can just be made by expensive equipment, and it is higher to prepare cost, and the poor mechanical property of film, limit its
Application on solid state device.
The content of the invention
The embodiment of the present invention provides a kind of thin polymer film and its system with changing color resulting from acid and aggregation-induced emission performance
Preparation Method, the thin polymer film not only have changing color resulting from acid performance and aggregation-induced emission performance, also good film forming characteristics.
A kind of preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance, the preparation method
Comprise the following steps：
Organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance；
The organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to obtain mixed liquor；
The mixed liquor is made by thin polymer film using liquid membrane formation process.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
The general structure of organic micromolecule compound is：
Wherein, R1Selected from H, alkali metal ion, C1~8Alkyl, acyl group, sulfonyl or phenyl；R2For direct singly-bound or aromatic radical, R3
For H or phenyl ring, R4、R5It is respectively selected from H, C1~8Alkyl, C1~4Alkoxy or aromatic radical.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Polymer includes one or more combinations in polystyrene, polymethyl methacrylate, polyvinyl chloride.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Solvent includes one or more combinations in dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Liquid membrane formation process is spin-coating method or pull-rod coating method.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
The percentage by weight of organic micromolecule compound and the polymer in the thin polymer film is：The organic molecule
Compound is between 0.01%-10%, and the polymer is between 90%-99.99%.
A kind of thin polymer film with changing color resulting from acid and aggregation-induced emission performance, the thin polymer film include：Have
Machine micromolecular compound and polymer, wherein, the organic micromolecule compound and the polymer are in the thin polymer film
In percentage by weight be：The organic micromolecule compound is between 0.01%-10%, and the polymer is between 90%-
Between 99.99%.
In the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention, the organic molecule
The general structure of compound is：
Wherein, R1Selected from H, alkali metal ion, C1~8Alkyl, acyl group, sulfonyl or phenyl；R2For direct singly-bound or aromatic radical, R3
For H or phenyl ring, R4、R5It is respectively selected from H, C1~8Alkyl, C1~4Alkoxy or aromatic radical.
In the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention, the polymer includes
One or more combinations in polystyrene, polymethyl methacrylate, polyvinyl chloride.
Thin polymer film of the present invention with changing color resulting from acid and aggregation-induced emission performance and preparation method thereof, leads to
Cross the organic micromolecule compound with changing color resulting from acid performance and aggregation-induced emission performance and gathering with excellent film forming
Compound mixed dissolution, and thin polymer film is made in mixed liquor, wherein, the thin polymer film include organic micromolecule compound and
Polymer, it not only has obvious changing color resulting from acid performance and aggregation-induced emission performance, and has excellent film forming；Separately
Outside, the preparation method of the thin polymer film, its technique is simple, and it is relatively low to prepare cost.
Brief description of the drawings
.Technical scheme in order to illustrate the embodiments of the present invention more clearly, required in being described below to embodiment
The accompanying drawing used is briefly described, it should be apparent that, drawings in the following description are only some embodiments of the present invention, right
For those skilled in the art, on the premise of not paying creative work, it can also be obtained according to these accompanying drawings other
Accompanying drawing.
Fig. 1 is the preparation side of the polymer provided in an embodiment of the present invention with changing color resulting from acid and aggregation-induced emission performance
The step schematic diagram of method.
Embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete
Site preparation describes.Obviously, described embodiment is only part of the embodiment of the present invention, rather than whole embodiments.It is based on
Embodiment in the present invention, the every other implementation that those skilled in the art are obtained under the premise of creative work is not made
Example, belongs to the scope of protection of the invention.
Referring to Fig. 1, Fig. 1 is the polymerization provided in an embodiment of the present invention with changing color resulting from acid and aggregation-induced emission performance
The step schematic diagram of the preparation method of thing.As shown in figure 1, provided in an embodiment of the present invention there is changing color resulting from acid and aggregation inducing to send out
The preparation method of the thin polymer film of optical property, the preparation method comprise the following steps：
Step S101, organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance；
Step S102, the organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to be mixed
Liquid；
Step S103, the mixed liquor is made by thin polymer film using liquid membrane formation process.
Specifically, in step S101, the general structure of the organic micromolecule compound is：
Wherein, R1Selected from H, alkali metal ion, C1~8Alkyl, acyl group, sulfonyl or phenyl；R2For direct singly-bound or aromatic radical, R3
For H or phenyl ring, R4、R5It is respectively selected from H, C1~8Alkyl, C1~4Alkoxy or aromatic radical.It is worth noting that, the organic molecule
Compound has changing color resulting from acid performance and aggregation-induced emission performance, and it is weaker that it launches fluorescence in the solution, but in state of aggregation
Or during solid, intense fluorescence can be launched.
In step s 102, will there is changing color resulting from acid and the organic molecule of aggregation-induced emission performance in step S101
Compound is with having the polymer of excellent film forming as mixed dissolution in solvent, to obtain mixed liquor.
Wherein, the polymer referred in the embodiment of the present invention need to have good film forming, so that by the polymer with having
Machine micromolecular compound mixed dissolution, can obtain one has changing color resulting from acid performance, aggregation-induced emission performance and excellent film forming
Mixed liquor.
The polymer includes one or more combinations in polystyrene, polymethyl methacrylate, polyvinyl chloride.Example
Such as, the polymer can be polystyrene, polymethyl methacrylate or polyvinyl chloride；The polymer can be polystyrene and poly- first
The mixing of base methyl acrylate；The polymer can be the mixing of polystyrene and polyvinyl chloride；The polymer can be poly- methyl-prop
The mixing of e pioic acid methyl ester and polyvinyl chloride；The polymer can be the mixed of polystyrene, polymethyl methacrylate and polyvinyl chloride
Close.It should be noted that polymer of the present invention be not only confined to it is described above, those skilled in the art according to
The polymer that polymer property described above is replaced, belongs to the scope of protection of the invention.
Wherein, the solvent referred in the embodiment of the present invention needs that micromolecular compound and polymer can be dissolved simultaneously, and
The solvent is volatile, can dissolve micromolecular compound and mixed with polymers to obtain mixed liquor, and in follow-up film forming procedure,
Because the solvent has volatility, and then manufactured thin polymer film is caused to only include organic micromolecule compound and polymer.
The solvent includes one or more combinations in dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran.Example
Such as, the solvent can be dichloromethane, chloroform, carbon tetrachloride or tetrahydrofuran；The solvent can be dichloromethane, three chloromethanes
Any two kinds of mixing in alkane, carbon tetrachloride, tetrahydrofuran；The solvent can be dichloromethane, chloroform, carbon tetrachloride, four
Any three a variety of mixing in hydrogen furans；The solvent can be the mixed of dichloromethane, chloroform, carbon tetrachloride and tetrahydrofuran
Close.It should be noted that solvent of the present invention be not only confined to it is described above, those skilled in the art according to
The solvent that the solvent properties of upper description are replaced, belongs to the scope of protection of the invention.
In step s 103, thin polymer film is made in the mixed liquor in step S102 using with liquid membrane formation process.Wherein,
The liquid membrane formation process can be spin-coating method or pull-rod coating method.In addition, in manufactured thin polymer film, organic molecule chemical combination
The percentage by weight of thing and polymer in thin polymer film is：Organic micromolecule compound gathers between 0.01%-10%
Compound is between 90%-99.99%.
Below by way of specific examples of the implementation, the invention will be further elaborated, but the present invention is not limited thereto particular case
Son.
Embodiment 1
(1) organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance：
By 2- amino -5- methoxybenzenethiols (6.20g, 40.00mmol) and tetraphenyl ethylene list aldehyde (14.40g,
40.00mmol) and 40.0mL dimethyl sulfoxide (DMSO)s are added in 250.0mL round-bottomed flask, are warming up to 170 DEG C, after reacting 12h
Room temperature is cooled to, reaction solution is poured into water, with dichloromethane extraction three times, organic layer anhydrous sodium sulfate drying, decompression rotation
Solvent is evaporated off, using the Methods For Purification of silica gel column chromatography, i.e., using dichloromethane and n-hexane volume ratio as 1:3 leacheate enters
Row column chromatography for separation, vacuum rotary steam remove solvent, vacuum drying, obtain 10.40g light yellow solids, wherein, the light yellow solid
For 6- methoxyl group -2- tetraphenyl ethylenes base-benzothiazole.
(2) organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to obtain mixed liquor：
Take 6- methoxyl group -2- tetraphenyl ethylenes base-benzothiazole (2.48g, 0.005mol) to be placed in 500mL conical flasks, add
Enter 100mL dichloromethane, while add polystyrene (97.52g), fully dissolved, obtained faint yellow with magnetic stirrer
Transparent mixed liquor.
(3) mixed liquor is made by thin polymer film using liquid membrane formation process：
After the pale yellow transparent mixed liquor is sealed into static 2h, mixed liquor whirler spin-coating dries in the air film
It is dry, so as to obtain thin polymer film.
Embodiment 2
(1) organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance：
Under an argon atmosphere, dichloromethane (16.0mL) solution that will contain BBr3 (8.00g, 32.00mmol) is slowly added to
To the dichloromethane (150.0mL) of -78 DEG C of -2- of methoxyl group containing 6- tetraphenyl ethylenes base-benzothiazole (7.92g, 64.00mmol)
In solution, stirred when being added dropwise, then be slowly increased to room temperature, react 24h.Water terminating reaction is added into reaction solution, uses dichloromethane
Alkane is extracted three times, and collected organic layer is simultaneously removed solvent, utilized the method for silica gel column chromatography with anhydrous sodium sulfate drying, vacuum rotary steam
Purification, i.e., carry out column chromatography for separation using dichloromethane as leacheate, and vacuum rotary steam removes solvent, vacuum drying, obtains 5.20g
Light yellow solid, wherein, the light yellow solid is 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole.
(2) organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to obtain mixed liquor：
Take 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole 1.60g to be placed in 500mL conical flasks, add 100mL dichloromethanes
Alkane, while polystyrene (98.40g) is added, fully dissolved with magnetic stirrer, obtain pale yellow transparent mixed liquor.
(3) mixed liquor is made by thin polymer film using liquid membrane formation process：
After the pale yellow transparent mixed liquor is sealed into static 2h, mixed liquor whirler spin-coating dries in the air film
It is dry, so as to obtain thin polymer film.
Embodiment 3
(1) organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance：
By 2- amino -5- methoxybenzenethiols (6.20g, 40.00mmol) and tetraphenyl ethylene list aldehyde (14.40g,
40.00mmol) and 40.0mL dimethyl sulfoxide (DMSO)s are added in 250.0mL round-bottomed flask, are warming up to 170 DEG C, after reacting 12h
Room temperature is cooled to, reaction solution is poured into water, with dichloromethane extraction three times, organic layer anhydrous sodium sulfate drying, decompression rotation
Solvent is evaporated off, using the Methods For Purification of silica gel column chromatography, i.e., using dichloromethane and n-hexane volume ratio as 1:3 leacheate enters
Row column chromatography for separation, vacuum rotary steam remove solvent, vacuum drying, obtain 10.40g light yellow solids, wherein, the light yellow solid
For 6- methoxyl group -2- tetraphenyl ethylenes base-benzothiazole.
(2) organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to obtain mixed liquor：
Take 6- methoxyl group -2- tetraphenyl ethylenes base-benzothiazole 7.44g to be placed in 500mL conical flasks, add 100mL dichloros
Methane, while polystyrene (92.56g) is added, fully dissolved with magnetic stirrer, obtain pale yellow transparent mixed liquor.
(3) mixed liquor is made by thin polymer film using liquid membrane formation process：
After the pale yellow transparent mixed liquor is sealed into static 2h, mixed liquor whirler spin-coating dries in the air film
It is dry, so as to obtain thin polymer film.
Embodiment 4
(1) organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance：
Under an argon atmosphere, dichloromethane (16.0mL) solution that will contain BBr3 (8.00g, 32.00mmol) is slowly added to
To the dichloromethane (150.0mL) of -78 DEG C of -2- of methoxyl group containing 6- tetraphenyl ethylenes base-benzothiazole (7.92g, 64.00mmol)
In solution, stirred when being added dropwise, then be slowly increased to room temperature, react 24h.Water terminating reaction is added into reaction solution, uses dichloromethane
Alkane is extracted three times, and collected organic layer is simultaneously removed solvent, utilized the method for silica gel column chromatography with anhydrous sodium sulfate drying, vacuum rotary steam
Purification, i.e., carry out column chromatography for separation using dichloromethane as leacheate, and vacuum rotary steam removes solvent, vacuum drying, obtains 5.20g
Light yellow solid, wherein, the light yellow solid is 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole.
(2) organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to obtain mixed liquor：
Take 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole 3.20g to be placed in 500mL conical flasks, add 100mL dichloromethanes
Alkane, while polystyrene (96.80g) is added, fully dissolved with magnetic stirrer, obtain pale yellow transparent mixed liquor.
(3) mixed liquor is made by thin polymer film using liquid membrane formation process：
After the pale yellow transparent mixed liquor is sealed into static 2h, mixed liquor whirler spin-coating dries in the air film
It is dry, so as to obtain thin polymer film.
The preparation method of thin polymer film of the present invention with changing color resulting from acid and aggregation-induced emission performance, passes through
By the organic micromolecule compound with changing color resulting from acid performance and aggregation-induced emission performance and polymerizeing with excellent film forming
Thing mixed dissolution, and thin polymer film is made in mixed liquor, wherein, the thin polymer film includes organic micromolecule compound and gathered
Compound, it not only has obvious changing color resulting from acid performance and aggregation-induced emission performance, and has excellent film forming；Separately
Outside, the preparation method of the thin polymer film, its technique is simple, and it is relatively low to prepare cost.
Claims (9)
- A kind of 1. preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance, it is characterised in that institute Preparation method is stated to comprise the following steps：Organic micromolecule compound of the synthesis with changing color resulting from acid and aggregation-induced emission performance；The organic micromolecule compound and polymer are placed in mixed dissolution in solvent, to obtain mixed liquor；The mixed liquor is made by thin polymer film using liquid membrane formation process.
- 2. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance Method, it is characterised in that the general structure of the organic micromolecule compound is：Wherein, R1Selected from H, alkali metal ion, C1~8Alkyl, acyl group, sulfonyl or phenyl；R2For direct singly-bound or aromatic radical, R3 For H or phenyl ring, R4、R5It is respectively selected from H, C1~8Alkyl, C1~4Alkoxy or aromatic radical.
- 3. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance Method, it is characterised in that the polymer includes the one or more in polystyrene, polymethyl methacrylate, polyvinyl chloride Combination.
- 4. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance Method, it is characterised in that the solvent includes one or more in dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran Combination.
- 5. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance Method, it is characterised in that the liquid membrane formation process is spin-coating method or pull-rod coating method.
- 6. the thin polymer film with changing color resulting from acid and aggregation-induced emission performance according to claim any one of 1-5 Preparation method, it is characterised in that the weight of the organic micromolecule compound and the polymer in the thin polymer film Percentage is：The organic micromolecule compound between 0.01%-10%, the polymer between 90%-99.99% it Between.
- A kind of 7. thin polymer film with changing color resulting from acid and aggregation-induced emission performance, it is characterised in that the polymer thin Film includes：Organic micromolecule compound and polymer, wherein, the organic micromolecule compound and the polymer are described poly- Percentage by weight in compound film is：Between 0.01%-10%, the polymer is situated between the organic micromolecule compound Between 90%-99.99%.
- 8. the thin polymer film according to claim 7 with changing color resulting from acid and aggregation-induced emission performance, its feature exist In the general structure of the organic micromolecule compound is：Its In, R1Selected from H, alkali metal ion, C1~8Alkyl, acyl group, sulfonyl or phenyl；R2For direct singly-bound or aromatic radical, R3For H or benzene Ring, R4、R5It is respectively selected from H, C1~8Alkyl, C1~4Alkoxy or aromatic radical.
- 9. the thin polymer film according to claim 7 with changing color resulting from acid and aggregation-induced emission performance, its feature exist In the polymer includes one or more combinations in polystyrene, polymethyl methacrylate, polyvinyl chloride.
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Cited By (2)
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